TV & Movies

Ask Sharleen: Should I Disclose a Past Hookup?

Sharleen Joynt—opera singer, FLARE columnist, Bachelor alum and all-around cool girl—answers your most pressing love queries. This month: whether to come clean about a past hook-up... with his childhood friend

Sharleen Joynt Bachelor FLARE

Sharleen Joynt (Illustration: Spiros Halaris)


Past Fun = Future Complication?
I’m dating someone, and it’s getting serious. I recently learned that one of his best friends since childhood is a person I had fun with in the past. We just hooked up, so it was never serious, but now I’m scared this will jeopardize what I’m building with my guy. I’m not sure if I should tell him—or how—because I’m not prepared for the consequences. What should I do?

Sharleen: While I don’t always believe honesty is the best policy, honesty is usually the best policy, and in your situation, it’s the only viable option. There are many reasons why. First, if your man and his childhood friend really are close, it’s only a matter of time before he finds out. The worst-case scenario is he learns about it from anyone but you. Telling him as soon as possible is as much about full disclosure as it is about damage control.

Second, even if your guy never finds out, the topic will forever be a source of anxiety for you. So if only for your peace of mind, tell him.

Above all, it’s a matter of treating your man the way you’d want to be treated. (And be honest: if the tables were turned, would you be fine with it? Don’t expect a reaction that you yourself couldn’t give.) OK, so it’s possible he may not love this information, but if he cares about you, he’ll get over it. Being kept in the dark is a different beast. Secrecy is a far worse red flag than any casual romp, and frankly, while he’d have no real reason to be mad about the actual hookup, he would definitely be justified in being upset if you hid it from him.

Tell him the truth, and repeat what you’ve told me: you were nervous to tell him and hadn’t mentioned it sooner because you didn’t want to jeopardize the good thing you have going. If the two of you are indeed a great match, he won’t get hung up on this. If he does, that unto itself is a red flag. Needless jealousy—especially when the cause is in the past—is never good.

More from Sharleen Joynt (who, BTW, will be recapping JoJo Fletcher’s turn as Bachelorette starting May 24):
When Does Sharing Become TMI
My Friend is a Train Wreck, Should I Stop Her?
When Should I Stop Making the Next Move?
My BF Is a Heavy Pot-Smoker, Should I Leave Him?
How Do I Get Back in the Dating Game After Years?
Dating Rich and Ditching the Friend Zone
Why Is My BF Icing Me Out on Social?